The Chrysler 200 Convertible is a mainstay in sunny-weather rental-car fleets, and while you might think that's a positive association for the model, it's bad news for value. Chrysler has pushed these models out to fleets in numbers far greater than their demand; they then flood the wholesale used-car market later when they're taken out of duty, bringing prices way down for anyone who paid retail. And that name change from Sebring to 200 a few years back? Didn't change values at all.

Chevrolet ImpalaBase MSRP: $26,685Worth this percent of its original value after 5 years: 25

The 2013 Chevrolet Impala runs on some very old bones—in the form of a platform that dates back to the 1980s. Although GM has refreshed it a few times over the years, even those who aren't automotive enthusiasts will spot this as an odd holdover, and a model that's been minted past its time, quietly filling rental-car fleets and agency lots. Pushing the value of the ancient-looking 2013 model (to just a quarter of its MSRP after five years) is the knowledge that an all-new 2014 Impala is on the way this spring.